Chloroform → HCID 46941455, compound

HRID 1725495Notes

Reaction equation

HRID 1725495 reaction equation
N[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.[N+]([O-])(OC(C)(C)C)=O.C(=O)(O)[O-].[Na+].C(Cl)(Cl)[Cl:34]>[Cu](Cl)Cl>[CH2:13]([O:12][C:4]1[CH:3]=[C:2]([Cl:34])[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 516892Sodium BicarbonateHCID 46941457HCID 46941457, compound

Product 1

HCID 46941455HCID 46941455, compound

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

To a solution of 258 mg of methyl 6-amino4-(benzyloxy)pyridine-2-carboxylate dissolved in 5 ml of chloroform, 170 mg of tert-butyl nitrate and 210 mg of copper(II) chloride were added, and the mixture was stirred for 6 hours with the light being shut out. Then saturated sodium bicarbonate was added to the resulting reaction mixture, and then the mixture was extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure. The resulting residue was purified by flash chromatography (eluent: hexane/ethyl acetate) to yield the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under a reduced pressure
  3. customThe resulting residue was purified by flash chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-93e19dcf230c413bb516f8832692954d
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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